NP-MRD: Showing NP-Card for 8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol (NP0256700)

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Record Information

Version

2.0

Created at

2022-09-07 21:36:53 UTC

Updated at

2022-09-07 21:36:53 UTC

NP-MRD ID

NP0256700

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol

Description

Camelliagenin A, also known as barrigenol A2 or theasapogenin I, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Camelliagenin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Camelliagenin A has been detected, but not quantified in, fats and oils and tea. 8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol is found in Barringtonia asiatica, Camellia japonica, Camellia sinensis, Harpullia pendula, Pittosporum angustifolium, Polaskia chichipe and Primula japonica. This could make camelliagenin a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307522D          

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M  END

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M  END


  Mrv0541 05061307522D          

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    4.0493    0.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7637    0.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1927    1.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6216    1.4970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4769   -0.9780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7276    1.9958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9071    0.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 18  8  2  0  0  0  0
 19 14  1  0  0  0  0
 19 18  1  0  0  0  0
 20 10  1  0  0  0  0
 21  9  1  0  0  0  0
 22 11  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 25  1  1  0  0  0  0
 25  2  1  0  0  0  0
 25 14  1  0  0  0  0
 25 15  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 20  1  0  0  0  0
 26 22  1  0  0  0  0
 27  5  1  0  0  0  0
 27 12  1  0  0  0  0
 27 20  1  0  0  0  0
 27 21  1  0  0  0  0
 28  6  1  0  0  0  0
 28 13  1  0  0  0  0
 28 21  1  0  0  0  0
 29  7  1  0  0  0  0
 29 16  1  0  0  0  0
 29 18  1  0  0  0  0
 29 28  1  0  0  0  0
 30 17  1  0  0  0  0
 30 19  1  0  0  0  0
 30 23  1  0  0  0  0
 30 24  1  0  0  0  0
 31 17  1  0  0  0  0
 32 22  1  0  0  0  0
 33 23  1  0  0  0  0
 34 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256700

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC(O)C2(CO)C(O)CC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O4/c1-25(2)14-19-18-8-9-21-27(5)12-11-22(32)26(3,4)20(27)10-13-28(21,6)29(18,7)16-24(34)30(19,17-31)23(33)15-25/h8,19-24,31-34H,9-17H2,1-7H3

> <INCHI_KEY>
CTNHZEZBBGIUJB-UHFFFAOYSA-N

> <FORMULA>
C30H50O4

> <MOLECULAR_WEIGHT>
474.7156

> <EXACT_MASS>
474.370910088

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
56.69184364625467

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-3,8,9-triol

> <ALOGPS_LOGP>
4.71

> <JCHEM_LOGP>
3.660747543666666

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.73819428405427

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.136103252585965

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351218782716149

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
136.71299999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.570   7.054   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.549   7.054   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.568  -3.005   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.547  -3.005   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.891   2.024   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.572   1.969   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.892  -0.286   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.559   3.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.225   2.794   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.225  -1.826   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.224   0.484   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.557   1.254   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.559  -1.056   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.226   5.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.893   5.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.226   0.484   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.893   2.024   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.892   2.794   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.226   3.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.891  -1.056   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.225   1.254   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.224  -1.056   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.893   3.564   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.560   1.254   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.560   5.874   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.557  -1.826   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.891   0.484   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.559   0.484   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.892   1.254   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.560   2.794   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.227   2.794   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.890  -1.826   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      14.425   3.725   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      12.893   0.484   0.000  0.00  0.00           O+0
CONECT    1   25                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7   29                                                            
CONECT    8    9   18                                                       
CONECT    9    8   21                                                       
CONECT   10   13   20                                                       
CONECT   11   12   22                                                       
CONECT   12   11   27                                                       
CONECT   13   10   28                                                       
CONECT   14   19   25                                                       
CONECT   15   23   25                                                       
CONECT   16   24   29                                                       
CONECT   17   30   31                                                       
CONECT   18    8   19   29                                                  
CONECT   19   14   18   30                                                  
CONECT   20   10   26   27                                                  
CONECT   21    9   27   28                                                  
CONECT   22   11   26   32                                                  
CONECT   23   15   30   33                                                  
CONECT   24   16   30   34                                                  
CONECT   25    1    2   14   15                                             
CONECT   26    3    4   20   22                                             
CONECT   27    5   12   20   21                                             
CONECT   28    6   13   21   29                                             
CONECT   29    7   16   18   28                                             
CONECT   30   17   19   23   24                                             
CONECT   31   17                                                            
CONECT   32   22                                                            
CONECT   33   23                                                            
CONECT   34   24                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
(3beta,16alpha,22alpha)-Olean-12-ene-3,16,22,28-tetrol	HMDB
Barrigenol a2	HMDB
Camelliasapogenol I	HMDB
Dihydropriverogenin a	HMDB
Proschiwalligenin pa2	HMDB
Theasapogenin I	HMDB
Theasapogenol D	HMDB
Chichipegenin	MeSH

Chemical Formula

C₃₀H₅₀O₄

Average Mass

474.7156 Da

Monoisotopic Mass

474.37091 Da

IUPAC Name

8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-3,8,9-triol

Traditional Name

8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol

CAS Registry Number

Not Available

SMILES

CC1(C)CC(O)C2(CO)C(O)CC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1

InChI Identifier

InChI=1S/C30H50O4/c1-25(2)14-19-18-8-9-21-27(5)12-11-22(32)26(3,4)20(27)10-13-28(21,6)29(18,7)16-24(34)30(19,17-31)23(33)15-25/h8,19-24,31-34H,9-17H2,1-7H3

InChI Key

CTNHZEZBBGIUJB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Barringtonia asiatica	LOTUS Database	35616633
Camellia japonica	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Harpullia pendula	LOTUS Database	35616633
Pittosporum angustifolium	LOTUS Database	35616633
Polaskia chichipe	LOTUS Database	35616633
Primula japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cyclic alcohol
Secondary alcohol
Polyol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.71	ALOGPS
logP	3.66	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	14.14	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	136.71 m³·mol⁻¹	ChemAxon
Polarizability	56.69 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034528

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013029

KNApSAcK ID

Not Available

Chemspider ID

532470

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

612548

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol (NP0256700)

MOL for NP0256700 (8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol)

3D MOL for NP0256700 (8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol)

3D SDF for NP0256700 (8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol)

3D-SDF for NP0256700 (8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol)

PDB for NP0256700 (8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol)

3D PDB for NP0256700 (8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol)

SMILES for NP0256700 (8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol)

INCHI for NP0256700 (8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol)

Structure for NP0256700 (8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol)

3D Structure for NP0256700 (8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8,9-triol)